[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1.[Cl:20][C:21]1[C:26](Cl)=[N:25][CH:24]=[CH:23][N:22]=1.O>CN(C=O)C>[Cl:20][C:21]1[C:26]([O:19][C@H:16]2[CH2:15][CH2:14][C@H:13]([NH:12][C:4]3[S:3][C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[N:5]=3)[CH2:18][CH2:17]2)=[N:25][CH:24]=[CH:23][N:22]=1Sodium hydride (60% dispersion, 0.41 g, 10.2 mmol) was added to a solution of trans-4-(benzo[d]thiazol-2-ylamino)cyclohexanol (as prepared according to Scheme 5) (1.10 g, 4.43 mmol) in DMF (20 mL) under argon. The mixture was stirred for 45 min and then 2,3-dichloropyrazine (0.66 g, 4.43 mmol) was added via syringe. This mixture was heated to 60° C. for 16 h, cooled to room temperature, then water was added slowly. The resulting suspension was filtered and the collected solid was purified by silica gel chromatography to give N-(trans-4-(3-chloropyrazin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine (0.92 g, 2.54 mmol, 57% yield) as a white solid.
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